This is a fictional city. What I need help with is finding a medieval city that has roughly the same shape. I want to get a sense of the surrounding geography in order to create my regional map around the city. There is a estuary or large river to the south running from west to east. The smaller network surrounding the city or leading north can be ignored.

I'm voting to close this question as off-topic because it is about real-world historical and geographical research.
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doppelgreenerJul 9 at 13:35

@doppelgreener Prep work for many RPGs involve looking at real-world historical and geographical research. The difference is that the answer that historians give is not always in a gamable form. Asked here it likely will be in a form useful to a game. This site is a Q&A is about RPGs which are not just a bag of rules but also involves developing, prepping, and running campaigns, setting, and adventures. I was working a city for a RPG campaign and wanted an answer useful for a game hence I asked it here.
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RS ConleyJul 9 at 15:11

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It is definitely around the border of real world research questions that fit well here. On one hand, the primary criteria of the question is: "find me a real world city that looks like this", which requires no RPG expertise at all to determine, and requires a very different set of expertise. On the other hand, you want to do some RPG development with it. It is hard to judge what side of the border it fits on, but I do not think our RPG expertise is sufficiently relevant and leveraged to call this question on topic.
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doppelgreenerJul 9 at 15:38

@doppelgreener I disagree in that developing settings are part of RPGs. A lot of setting prep involves kitbashing real world information. Given this I felt I had a good shot of finding an answer as it happens there are two good answers on this question. And in the past I had negative experience trying to ask these types of question on the history forums. Even something as simple as "What are medieval sheepfolds used for in herding?" got closed. My view is that given the flexibility of RPGs these question are on-topic as long as they are clearly related to prep which this one was.
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RS ConleyJul 9 at 15:51

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"My view is that given the flexibility of RPGs these question are on-topic as long as they are clearly related to prep which this one was." - That is not our current policy: real world research questions are on topic as long as they relate to RPG expertise (and an RPG expert would provide a better/different/more specific answer). Whether it's being used in prep doesn't affect whether it stays open or closed, and many questions about real-world research for the sake of prep have been closed.
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doppelgreenerJul 9 at 23:07

Good fit. Shame most of the maps I've found (and yours too) have fortifications alla moderna
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TsojcanthAug 27 '10 at 11:00

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@Tsojcanth : The map is from the 16th century, after many additions. The river changed its course as from a violent earthquake in 12th century. The initial core of the city was even closer to what the OP asks for, but I am unable to find any map of the original Castrum on the net. The OP can search for books about Ferrara for a closer match.
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Stefano BoriniAug 27 '10 at 11:05

I'm trying but it's gonna be difficult with a road network so perfect.

Anyway, depending on how you're willing to stray:

Frankfur Am Main is the best fit i found, if you add/ignore the bastion w/walled area on the other side (source)

Aosta is really good too, except the big river is a bit further away. Roman founded cities built by a river are good candidates because of the square-shaped castra they were built around.

Milan has a lateral citadel like your map, with no river/harbour by it and a circular rather than square shape, but lots of canals. The internal circle is the edge of the Gaelic and then Roman city (not founded by Romans, so no square city centre). Map linked is late and showing modern Italian style (post-firearm) fortifications.

I have no literature here, but I suggest you check fortress and cities built by the Teutonic Knights on rivers in Prussia. Osprey publishes two books on "Crusader Castles of the Teutonic Knights" that might be helpfful.

London, as also RSConley mentions, is probably the best fit. It also has a citadel quite close to the river :) (two maps here)